Sail training voyages have been shown to enhance self-constructs and inter-personal and intra-personal skills. It is suggested through this case-study approach with twelve 14 year-old crew participants that such an experience contributes towards well-being and character development in emerging adulthood. An audit of voyage-based experiences generated an inventory of 58 authentic activities and participants completed questionnaires immediately post-voyage (T[superscript 1]) and six months later (T[superscript 2]) to rate the significance of each activity. The highest rated activities reflected Maslow's lower order of needs with a two-thirds correspondence at T[superscript 1] and T[superscript 2]. Helming (or steering the vessel) was ranked as the most significant activity by participants in both time periods, although participants had questioned their ability to do this before the voyage. Helming is suggested to activate cognitive, psychomotor and affective domains in an authentic adventure education experience that contributes to hedonic well-being and may provide a course towards eudaimonia.